Task-specific ionic liquid as base, ligand and reaction medium for the palladium-catalyzed Heck reaction

被引：106

作者：

Wang, Lei ^{[1
,2
]}

Li, Hongji ^{[1
]}

Li, Pinhua ^{[1
]}

机构：

[1] Huaibei Coal Teachers Coll, Dept Chem, Huaibei 235000, Anhui, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2009年 / 65卷 / 01期

基金：

中国国家自然科学基金;

关键词：

Heck reaction; Task-specific ionic liquid (TSIL); Ethanolamine-functionalized quaternary ammonium salt; 4-Di(hydroxyethyl)aminobutyl tributylammonium bromide (DHEABTBAB); AMINO-ALCOHOL LIGANDS; HIGHLY EFFICIENT; ENANTIOSELECTIVE ADDITION; TRANSFER HYDROGENATION; ASYMMETRIC-SYNTHESIS; RECYCLABLE CATALYST; HALIDES; ALKYNYLATION; DIALKYLZINC; DIETHYLZINC;

D O I：

10.1016/j.tet.2008.10.042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel ionic liquid, which was based on ethanolamine-functionalized quaternary ammonium salt was designed and synthesized. 4-Di(hydroxyethyl)aminobutyl tributylammonium bromide (DHEABTBAB) 1, a task-specific ionic liquid, which acts as a base, ligand and reaction medium, exhibits a very high activity and recyclability to palladium-catalyzed Heck reaction. The olefinations of iodoarenes, bromoarenes and chloroarenes with olefins generated the corresponding cross-coupling products in good to excellent yields only in the presence of DHEABTBAB and palladium acetate under phosphine-free reaction conditions. It is noteworthy that palladium and DHEABTBAB could be repeatedly recycled and reused for six consecutive trials without significant loss of their activities. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：364 / 368

页数：5

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